| 100% | IAM | 3 | "___ Sam" (Sean Penn/Dakota Fanning film) (2 wds.) |
| 85% | IAMSAM | 6 | 2001 Sean Penn/Dakota Fanning film: 3 wds. |
| 80% | IAM | 3 | "___ Sam" (Sean Penn/Dakota Fanning movie) (2 wds.) |
| 74% | IAM | 3 | Sean Penn starrer "___ Sam": 2 wds. |
| 74% | IAM | 3 | Sean Penn's "___ Sam": 2 wds. |
| 61% | IAM | 3 | "___ Sam" (2001 movie starring Sean Penn): 2 wds. |
| 60% | IAM | 3 | "___ Sam" (Sean Penn movie): 2 wds. |
| 57% | IAM | 3 | "___ Sam" (Dakota Fanning starrer): 2 wds. |
| 53% | CHARLOTTESWEB | 13 | Julia Roberts/Dakota Fanning film based on a novel by E.B. White (2 wds.) |
| 52% | IAMSAM | 6 | 2001 Sean Penn film whose title was inspired by "Green Eggs and Ham": 3 wds. |
| 51% | DENNISLEHANE | 12 | Author of the 2001 novel "Mystic River" that was made into a 2003 Sean Penn film: 2 wds. |
| 49% | JILLARRINGTON | 13 | Female sportscaster who is the aunt of actress Dakota Fanning: 2 wds. |
| 49% | MYSTICRIVER | 11 | 2003 movie set in Boston, for which Sean Penn and Tim Robbins each won a 1-Across: 2 wds. |
| 47% | THEMOON | 7 | "Racing With ___," drama film featuring Sean Penn as Henry Nash whose title is also a Vaughn Monroe song: 2 wds. |
| 46% | IAMSAM | 6 | 2001 Sean Penn film |
| 46% | DRNO | 4 | James Bond film starring Sean Connery: 2 wds. |
| 46% | DRNO | 4 | First 007 film starring Sean Connery: 2 wds. |
| 46% | IAMSAM | 6 | Sean Penn film with a Seussian title |
| 46% | PIZZA | 5 | “Licorice ___” (2021 Sean Penn film) |
| 45% | THEALIENIST | 11 | American period drama TV series starring Dakota Fanning which is based on a novel of the same name by Caleb Carr: 2 wds. |
| 45% | DAKOTAFANNING | 13 | Sean Penn's daughter in "I Am Sam" |
| 45% | MAN | 3 | "Dead ___ Walking" (1995 Sean Penn film) |
| 45% | RED | 3 | "The Thin __ Line"; Sean Penn film |
| 44% | ONA | 3 | Sam Worthington thriller film "Man ___ Ledge": 2 wds. |
| 44% | DRNO | 4 | Sean Connery's first Bond film (2 wds.) |
| 44% | TREE | 4 | "The ___ of Life" (2011 Sean Penn film) |
| 44% | SAM | 3 | Sean Penn starrer drama film "I Am ___" |
| 43% | ISNOT | 5 | "The World ___ Enough": 2 wds. (James Bond film) |
| 43% | DRNO | 4 | 1962 007 film: 2 wds. |
| 43% | DRNO | 4 | First 007 film: 2 wds. |